4-chloro-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidin-2-amine → N4-{2-[(2-aminopyrimidin-4-yl)amino]ethyl}-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidine-2,4-diamine

HRID 2386978ノート

反応式

HRID 2386978 の反応式
Cl.Cl.[NH2:3][CH2:4][CH2:5][NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([NH2:13])[N:8]=1.Cl[C:15]1[C:16]2[CH2:26][CH2:25][CH2:24][C:23]3[CH:27]=[CH:28][CH:29]=[CH:30][C:22]=3[C:17]=2[N:18]=[C:19]([NH2:21])[N:20]=1>COCCO.[OH-].[Na+]>[NH2:13][C:9]1[N:8]=[C:7]([NH:6][CH2:5][CH2:4][NH:3][C:15]2[C:16]3[CH2:26][CH2:25][CH2:24][C:23]4[CH:27]=[CH:28][CH:29]=[CH:30][C:22]=4[C:17]=3[N:18]=[C:19]([NH2:21])[N:20]=2)[CH:12]=[CH:11][N:10]=1

参加物

5

反応物 2

HCID 866218984-chloro-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidin-2-amineHCID 86638141N4-(2-aminoethyl)pyrimidine-2,4-diamine dihydrochloride

生成物 1

HCID 44609408N4-{2-[(2-aminopyrimidin-4-yl)amino]ethyl}-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidine-2,4-diamine

試薬・触媒・溶媒 2

HCID 80192-Methoxyethanol溶媒HCID 14798Sodium Hydroxide溶媒

反応条件

温度
130 °C

実験手順

The product of Example 1E (155 mg, 0.686 mmol) and the product of Example 1C (140 mg, 0.571 mmol) were combined in 2-methoxyethanol (0.8 mL) and heated to 130° C. for three hours. The mixture was diluted with 1 N aqueous sodium hydroxide and extracted twice with methylene chloride. The organic layers were combined and dried over sodium sulfate and the mixture was absorbed on silica gel and purified using silica gel chromatography, eluting with a gradient of 7 N ammonia in methanol in methylene chloride (5-15%) to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.62 (d, J=4.41 Hz, 1H) 7.50-7.56 (m, 1H) 7.26-7.34 (m, 2H) 7.19-7.26 (m, 1H) 6.67-6.75 (m, 1H) 5.85 (s, 2H) 5.70-5.81 (m, 4H) 3.37-3.52 (m, 4H) 2.44 (t, J=6.78 Hz, 2H) 2.08-2.18 (m, J=6.78, 6.78 Hz, 2H) 1.92-2.04 (m, 2H); MS (ESI+) m/z 363.9 (M+H)+.

後処理

  1. extractionextracted twice with methylene chloride
  2. dry with materialdried over sodium sulfate
  3. customthe mixture was absorbed on silica gel
  4. custompurified
  5. washeluting with a gradient of 7 N ammonia in methanol in methylene chloride (5-15%)

出典と根拠

ORDレコード
ord-58741ababeab4221b9dc1aef513a1670
出典データセット
uspto-grants-2012_09
特許番号
US08268846B2

反応ノート

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